Trifluoroacetic acid → HCID 9888078, compound

HRID 723326Notes

Reaction equation

HRID 723326 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([C:21]1[CH:26]=[CH:25][C:24](OC2C=CC=CC=2)=[CH:23][CH:22]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)=[O:7].F[C:37](F)(F)[C:38]([OH:40])=O>>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([N:8]2[CH:3]=[CH:4][N:5]([C:21]3[CH:26]=[CH:25][C:24]([O:40][C:38]4[CH:37]=[CH:11][CH:10]=[CH:9][CH:14]=4)=[CH:23][CH:22]=3)[C:6]2=[O:7])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21873333HCID 21873333, compound

Product 1

HCID 9888078HCID 9888078, compound

Procedure

1-(2,2-Dimethoxyethyl)-3-[4-(2-dimethylaminoethoxy)phenyl]-1-(4-phenoxy-phenyl)urea (0.33 g) was shaken with trifluoroacetic acid (5 ml) for 16 hours. Volatiles were removed and the residue was taken up in dichloromethane (10 ml) and washed with sodium hydroxide solution (0.1N; 1 ml). The aqueous phase was extracted with dichloromethane (10 ml), and the combined organic phases were concentrated. The residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 98:2 with 1% v/v 7N ammonia solution in methanol). The product with the molecular weight of 415.50 (C25H25N3O3); MS (ESI): 416 ([M+H]+), was obtained in this way.

Workup

  1. customVolatiles were removed
  2. washwashed with sodium hydroxide solution (0.1N; 1 ml)
  3. extractionThe aqueous phase was extracted with dichloromethane (10 ml)
  4. concentrationthe combined organic phases were concentrated
  5. customThe residue was purified by chromatography on silica gel (eluent
  6. customMS (ESI): 416 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-bde9c62aaa9d46c4b3f850ce716c244d
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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